CA2424359A1 - Implants with a phosphazene-containing coating - Google Patents
Implants with a phosphazene-containing coating Download PDFInfo
- Publication number
- CA2424359A1 CA2424359A1 CA002424359A CA2424359A CA2424359A1 CA 2424359 A1 CA2424359 A1 CA 2424359A1 CA 002424359 A CA002424359 A CA 002424359A CA 2424359 A CA2424359 A CA 2424359A CA 2424359 A1 CA2424359 A1 CA 2424359A1
- Authority
- CA
- Canada
- Prior art keywords
- active agent
- artificial implant
- substrate
- implant according
- coating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000007943 implant Substances 0.000 title claims abstract 12
- 239000011248 coating agent Substances 0.000 title claims 9
- 238000000576 coating method Methods 0.000 title claims 9
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 title claims 2
- 239000013543 active substance Substances 0.000 claims 9
- 229920000642 polymer Polymers 0.000 claims 8
- 239000000758 substrate Substances 0.000 claims 7
- 230000002965 anti-thrombogenic effect Effects 0.000 claims 6
- 238000000034 method Methods 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000002318 adhesion promoter Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 108010035030 Platelet Membrane Glycoprotein IIb Proteins 0.000 claims 1
- 102000001788 Proto-Oncogene Proteins c-raf Human genes 0.000 claims 1
- 108010029869 Proto-Oncogene Proteins c-raf Proteins 0.000 claims 1
- GSNOZLZNQMLSKJ-UHFFFAOYSA-N Trapidil Chemical compound CCN(CC)C1=CC(C)=NC2=NC=NN12 GSNOZLZNQMLSKJ-UHFFFAOYSA-N 0.000 claims 1
- 229960000446 abciximab Drugs 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 230000001621 anti-mitogenic effect Effects 0.000 claims 1
- 230000000692 anti-sense effect Effects 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 claims 1
- 229960005110 cerivastatin Drugs 0.000 claims 1
- 239000000824 cytostatic agent Substances 0.000 claims 1
- 230000001085 cytostatic effect Effects 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000003961 organosilicon compounds Chemical group 0.000 claims 1
- 230000035515 penetration Effects 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 239000013612 plasmid Substances 0.000 claims 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims 1
- 229960003912 probucol Drugs 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229960000363 trapidil Drugs 0.000 claims 1
- 238000007704 wet chemistry method Methods 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
- A61L27/34—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/06—Use of macromolecular materials
- A61L33/068—Use of macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Abstract
The invention relates to artificial implants with a biocompatible surface which has antithrombitic properties, furthermore contains a pharmacologicall y active ingredient and a method for production thereof.
Claims (12)
1. Artificial implant comprising an implant material as the substrate and a biocompatible coating applied at least partly to the surface of the substrate, which coating comprises an antithrombogenic polymer having the following general formula (I) wherein R1 to R6 are the same or different and represent an alkoxy, alkylsulfonyl, dialkylamino or aryloxy group, or a heterocycloalkyl or heteroaryl group having nitrogen as the heteroatom, and at least one other pharmacologically active agent.
2. Artificial implant according to Claim 1, wherein at least one of the groups R1 to R6 is an alkoxy group substituted with at least one fluorine atom.
3. Artificial implant according to Claim 2, wherein the antithrombogenic polymer is poly[bis(trifluoroethoxy)phosphazene].
4. Artificial implant according to one of the Claims 1 to 3, wherein the other pharmacologically active agent is an antimitogenic active agent, especially a cytostatic, a PDGF antagonist, especially trapidil, or a Raf-1 kinase inhibitor.
5. Artificial implant according to one of the Claims 1 to 3, wherein the other pharmacologically active agent is a radical trap (especially probucol), an antisense active agent (especially plasmid DNA), a statin (especially cerivastatin) or a GP-IIb/IIIa receptor antagonist (especially abciximab).
6. Artificial implant according to one of the Claims 1 to 5, wherein the ratio of antithrombogenic polymer to active agent is from 1:0.0001 to 1:1, preferably from 1:0.05 to 1:0.5.
7. Artificial implant according to one of the Claims 1 to 6, wherein a layer containing an adhesion promoter is provided between the surface of the substrate and the biocompatible coating.
8. Artificial implant according to Claim 7, wherein the adhesion promoter is an organosilicon compound, especially aminopropyltrimethoxysilane.
9. Process for producing an artificial implant according to one of the Claims 1 to 8, wherein the biocompatible coating is applied to the substrate by reacting the substrate with (a) a mixture of the antithrombogenic polymer or a precursor of it and the active agent or (b) the antithrombogenic polymer or a precursor of it, to produce a primary polymer coating, and subsequent application/penetration of the active agent into the primary polymer coating.
10. Process according to Claim 9, wherein the coating is applied by wet chemistry, particularly by reacting the substrate with a mixture of antithrombogenic polymer and active agent.
11. Process according to Claim 10, wherein the solvent for the wet chemical application is selected from dipolar aprotic solvents and is preferably ethyl acetate.
12. Process according to Claims 9 to 11, wherein an adhesion promoter is applied to the surface of the substrate before the biocompatible coating is applied.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00117191.7 | 2000-08-11 | ||
EP00117191A EP1179353A1 (en) | 2000-08-11 | 2000-08-11 | Antithrombogenic implants with coating of polyphosphazenes and a pharmacologically active agent |
PCT/EP2001/008913 WO2002013882A1 (en) | 2000-08-11 | 2001-08-01 | Implants with a phosphazene-containing coating |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2424359A1 true CA2424359A1 (en) | 2003-02-06 |
CA2424359C CA2424359C (en) | 2012-03-20 |
Family
ID=8169492
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2424359A Expired - Lifetime CA2424359C (en) | 2000-08-11 | 2001-08-01 | Implants with a phosphazene-containing coating |
Country Status (13)
Country | Link |
---|---|
US (1) | US20030157142A1 (en) |
EP (2) | EP1179353A1 (en) |
JP (1) | JP4886156B2 (en) |
KR (1) | KR100809134B1 (en) |
CN (1) | CN100467073C (en) |
AT (1) | ATE374626T1 (en) |
AU (2) | AU9544701A (en) |
BR (1) | BR0113184B1 (en) |
CA (1) | CA2424359C (en) |
DE (1) | DE50113094D1 (en) |
DK (1) | DK1337285T3 (en) |
ES (1) | ES2296811T3 (en) |
WO (1) | WO2002013882A1 (en) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2001080919A2 (en) | 2000-04-11 | 2001-11-01 | Polyzenix Gmbh | Poly-tri-fluoro-ethoxypolyphosphazene coverings and films |
US20090004240A1 (en) * | 2000-08-11 | 2009-01-01 | Celonova Biosciences, Inc. | Implants with a phosphazene-containing coating |
DE10202467A1 (en) * | 2002-01-23 | 2003-07-24 | Polyzenix Gmbh | Device, useful as an artificial implant, comprises a substrate based on nitinol having at least a partial coating of a phosphazene polymer. |
DE10100961B4 (en) | 2001-01-11 | 2005-08-04 | Polyzenix Gmbh | Body-compatible material and substrate coated with this material for the cultivation of cells and artificial organic implants constructed or grown from cells |
US9080146B2 (en) | 2001-01-11 | 2015-07-14 | Celonova Biosciences, Inc. | Substrates containing polyphosphazene as matrices and substrates containing polyphosphazene with a micro-structured surface |
US20080228284A1 (en) * | 2001-01-11 | 2008-09-18 | Celonova Biosciences, Inc. | Specific Polyphosphazene-Containing Three-Dimensional Bone Support Implants and Methods for Their Use |
EP1432380B1 (en) | 2001-08-17 | 2006-09-27 | Polyzenix GmbH | Device based on nitinol with a polyphosphazene coating |
CA2491282C (en) * | 2002-07-05 | 2013-02-12 | Polyzenix Gmbh | Implant for transport and release for pharmacologically active agents incorporated within polyphosphazenes and related methods |
US20080138433A1 (en) * | 2002-07-05 | 2008-06-12 | Celonova Biosciences, Inc. | Vasodilator eluting blood storage and administration devices with a specific polyphosphazene coating and methods for their manufacture and use |
US20050136093A1 (en) * | 2002-07-05 | 2005-06-23 | Polyzenix Gmbh | Implant for transport and release for pharmacologically active agents as well as a process for producing the same |
DE602004030892D1 (en) * | 2003-03-26 | 2011-02-17 | Celonova Biosciences Germany Gmbh | COATED DENTAL IMPLANTS |
US9107850B2 (en) | 2004-10-25 | 2015-08-18 | Celonova Biosciences, Inc. | Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same |
US20210299056A9 (en) | 2004-10-25 | 2021-09-30 | Varian Medical Systems, Inc. | Color-Coded Polymeric Particles of Predetermined Size for Therapeutic and/or Diagnostic Applications and Related Methods |
US9114162B2 (en) | 2004-10-25 | 2015-08-25 | Celonova Biosciences, Inc. | Loadable polymeric particles for enhanced imaging in clinical applications and methods of preparing and using the same |
EP1804773B1 (en) * | 2004-10-25 | 2011-03-30 | CeloNova BioSciences Germany GmbH | Loadable polyphosphazene-comprising particles for therapeutic and/or diagnostic applications and methods of preparing and using the same |
CA2690539C (en) | 2006-10-10 | 2014-10-07 | Celonova Biosciences, Inc. | Bioprosthetic heart valve with polyphosphazene |
CN101032473B (en) * | 2007-04-05 | 2010-04-07 | 上海交通大学 | Sandwich type medical releasing film and preparing method thereof |
CA2687031A1 (en) * | 2007-05-15 | 2008-11-20 | Chameleon Biosurfaces Limited | Polymer coatings on medical devices |
CA2694408C (en) | 2007-07-25 | 2014-01-07 | Celonova Biosciences, Inc. | Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same |
DE102007038799A1 (en) * | 2007-08-17 | 2009-02-19 | Biotronik Vi Patent Ag | Implant made of a biocorrodible magnesium alloy and coated with a biocorrodible polyphosphazene |
WO2009110858A2 (en) * | 2007-10-31 | 2009-09-11 | Celonova Biosciences, Inc. | Vasodilator eluting dynamic blood handling devices with a specific polyphosphazene coating and methods for their manufacture and use |
WO2009058145A1 (en) * | 2007-10-31 | 2009-05-07 | Celonova Biosciences, Inc. | Vasodilator eluting luminal stent devices with a specific polyphosphazene coating and methods for their manufacture and use |
EP2252218A4 (en) * | 2008-02-11 | 2012-06-06 | Celonova Biosciences Inc | Tissue-fastening articles and devices, and related methods |
WO2009105761A2 (en) * | 2008-02-22 | 2009-08-27 | Celonova Biosciences, Inc. | Multi-functional wound dressing matrices and related methods |
US8579964B2 (en) | 2010-05-05 | 2013-11-12 | Neovasc Inc. | Transcatheter mitral valve prosthesis |
EP2616131A4 (en) * | 2010-09-16 | 2014-12-03 | Univ Kyoto | Statin-loaded coils for acceleration of organization after endovascular coiling of aneurysms |
US9308087B2 (en) | 2011-04-28 | 2016-04-12 | Neovasc Tiara Inc. | Sequentially deployed transcatheter mitral valve prosthesis |
US9554897B2 (en) | 2011-04-28 | 2017-01-31 | Neovasc Tiara Inc. | Methods and apparatus for engaging a valve prosthesis with tissue |
US9550011B2 (en) | 2012-05-03 | 2017-01-24 | Indiana University Research And Technology Corporation | Surface coatings for biological implants and prostheses |
US9345573B2 (en) | 2012-05-30 | 2016-05-24 | Neovasc Tiara Inc. | Methods and apparatus for loading a prosthesis onto a delivery system |
US9572665B2 (en) | 2013-04-04 | 2017-02-21 | Neovasc Tiara Inc. | Methods and apparatus for delivering a prosthetic valve to a beating heart |
CN113633435A (en) | 2016-01-29 | 2021-11-12 | 内奥瓦斯克迪亚拉公司 | Prosthetic valve for preventing outflow obstruction |
CN113893064A (en) | 2016-11-21 | 2022-01-07 | 内奥瓦斯克迪亚拉公司 | Methods and systems for rapid retrieval of transcatheter heart valve delivery systems |
CA3073834A1 (en) | 2017-08-25 | 2019-02-28 | Neovasc Tiara Inc. | Sequentially deployed transcatheter mitral valve prosthesis |
AU2019374743B2 (en) | 2018-11-08 | 2022-03-03 | Neovasc Tiara Inc. | Ventricular deployment of a transcatheter mitral valve prosthesis |
US11602429B2 (en) | 2019-04-01 | 2023-03-14 | Neovasc Tiara Inc. | Controllably deployable prosthetic valve |
WO2020210652A1 (en) | 2019-04-10 | 2020-10-15 | Neovasc Tiara Inc. | Prosthetic valve with natural blood flow |
CA3140925A1 (en) | 2019-05-20 | 2020-11-26 | Neovasc Tiara Inc. | Introducer with hemostasis mechanism |
AU2020295566B2 (en) | 2019-06-20 | 2023-07-20 | Neovasc Tiara Inc. | Low profile prosthetic mitral valve |
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-
2000
- 2000-08-11 EP EP00117191A patent/EP1179353A1/en not_active Withdrawn
-
2001
- 2001-08-01 JP JP2002519020A patent/JP4886156B2/en not_active Expired - Lifetime
- 2001-08-01 US US10/344,216 patent/US20030157142A1/en not_active Abandoned
- 2001-08-01 BR BRPI0113184-2A patent/BR0113184B1/en not_active IP Right Cessation
- 2001-08-01 CN CNB018173063A patent/CN100467073C/en not_active Expired - Lifetime
- 2001-08-01 KR KR1020037001952A patent/KR100809134B1/en not_active IP Right Cessation
- 2001-08-01 AU AU9544701A patent/AU9544701A/en active Pending
- 2001-08-01 AU AU2001295447A patent/AU2001295447B2/en not_active Expired
- 2001-08-01 EP EP01976054A patent/EP1337285B1/en not_active Expired - Lifetime
- 2001-08-01 WO PCT/EP2001/008913 patent/WO2002013882A1/en active IP Right Grant
- 2001-08-01 DK DK01976054T patent/DK1337285T3/en active
- 2001-08-01 CA CA2424359A patent/CA2424359C/en not_active Expired - Lifetime
- 2001-08-01 AT AT01976054T patent/ATE374626T1/en active
- 2001-08-01 DE DE50113094T patent/DE50113094D1/en not_active Expired - Lifetime
- 2001-08-01 ES ES01976054T patent/ES2296811T3/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
KR100809134B1 (en) | 2008-02-29 |
US20030157142A1 (en) | 2003-08-21 |
AU2001295447B2 (en) | 2007-01-04 |
BR0113184B1 (en) | 2014-12-02 |
ATE374626T1 (en) | 2007-10-15 |
AU9544701A (en) | 2002-02-25 |
WO2002013882A1 (en) | 2002-02-21 |
ES2296811T3 (en) | 2008-05-01 |
JP2004522461A (en) | 2004-07-29 |
EP1179353A1 (en) | 2002-02-13 |
DE50113094D1 (en) | 2007-11-15 |
CA2424359C (en) | 2012-03-20 |
CN1469759A (en) | 2004-01-21 |
CN100467073C (en) | 2009-03-11 |
JP4886156B2 (en) | 2012-02-29 |
KR20030061780A (en) | 2003-07-22 |
DK1337285T3 (en) | 2008-02-11 |
EP1337285A1 (en) | 2003-08-27 |
BR0113184A (en) | 2003-07-01 |
EP1337285B1 (en) | 2007-10-03 |
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